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Automated Remote Printing

If I've posted this in the wrong forum, please let me know.

I work for a small ecommerce business that runs our entire office and warehouse off of the backend of a heavily modified CRE Loaded shopping cart. We are trying to automate warehouse functions and are trying to solve the following problem.

We need to generate a picking list (preferably in HTML, open to other alternatives though) on our remotely hosted LAMP server and automatically print it in our warehouse. We need to size the picking list such that it fits on half a sheet of paper (5.5" x 8.5") and have it print on multiple pages if necessary.

We are currently accomplishing a similar task with our shipping labels by FTPing them to a folder on a Windows machine in our office that has a software program monitoring that folder and printing anything that gets dropped in it. This works fine with the shipping labels because they are images. However, when we try to do this with the picking list, we encounter the following problems:

1. Images included in the HTML file do not print, regardless of whether we try to load them remotely or FTP them into a directory relative to the HTML file.
2. Figuring out how to generate multiple pages for the picking list is difficult since the amount of content to write to each HTML file should vary based on the client rendering the HTML (in this case, the program that automatically prints anything in the folder).
3. Configuring the printer to use a non standard paper size is causing the printer to print more pages than is necessary.

We are open to any solutions to the problems above or any alternative approaches to generating multiple half page size documents on our server and automatically printing them in our warehouse. Thanks in advance for any input you have.